Steadman retired as Vice Chairman of the Chiefs on January 31, 2007 after being in the organization for over four decades, dating to their days as the American Football League's Dallas Texans.[1]

Steadman – the franchise’s first general manager – also served as executive vice president, president, vice chairman and chairman in his 47 years with the Chiefs. He won four championships as general manager including the team’s Super Bowl IV title.[1] Steadman and Lamar Hunt were at the forefront of the move to merge the AFL into the NFL.

In 1967, Kansas City was considering replacing its aging Municipal Stadium with a new multi-use stadium for both its baseball and football teams. Denver self-educated architect Charles Deaton suggested to Steadman that the teams would be better served if each sport had its own stadium that was configured to its unique demands but that the complex reduce costs by sharing parking and highway expenses. The architect firm Kivett and Myers perfected the plan (adding a rolling roof) and voters approved it. (The rolling roof, however, was never added.) Arrowhead Stadium opened in 1972 alongside Royals Stadium (now known as Kauffmann Stadium).

The rolling roof was not to be built but the concept established Kivett and its successors in Kansas City as the dominant architects for almost all single-purpose major leaguebaseball and football stadiums that have been built since. In 2005, the rolling roof plan re-emerged as part of Kansas City's bid to host Super Bowl XLIX, but the measure failed in the polls.

Steadman was named General Manager to Executive Vice President and General Manager in 1966; in August 1976 he was named President of the Chiefs; and in 1989 was named Chairman of the Board. During Steadman's term as President (1976–1989), the Chiefs entered a period of decline in which they never entered the playoffs for 15 years and only had four winning seasons.

In 2005, Steadman was inducted into the Chiefs Hall of Fame, the only executive other than Lamar Hunt to be honored with induction.[1] Also in 2005, Steadman was appointed as the club’s Vice Chairman of the Board where he served through the end of the 2006 season until his retirement.